1. Round
26/11/1938 Chester City - Bradford City 3:1
Darlington FC - Stalybridge Celtic 4:0
Bournemouth and Boscombe Athletic - Bristol City 2:1
Watford FC - Northampton Town 4:1
Reading FC - Newport County 3:3
Walsall FC - Carlisle United 4:1
Folkestone Invicta - Colchester United 2:1
Lincoln City - Barrow AFC 4:1
Gainsborough Trinity - Gateshead FC 2:1
Swindon Town - Lowestoft Town 6:0
Scarborough FC - Southport FC 0:0
Doncaster Rovers - New Brighton AFC 4:2
Wrexham AFC - Port Vale FC 1:2
Ipswich Town - Street FC 7:0
Bristol Rovers - Peterborough United 4:1
Bromley FC - Apsley FC 2:1
Hull City - Rotherham United 4:1
Clapton Orient - Hayes FC 3:1
Oldham Athletic - Crewe Alexandra 2:2
Crystal Palace - Queens Park Rangers 1:1
Southend United - Corinthian FC 3:0
Hartlepools United - Accrington Stanley 2:1
Scunthorpe & Lindsey - Lancaster City 4:2
Halifax Town - Rochdale AFC 7:3
Cheltenham Town - Cardiff City 1:1
Yeovil & Petters United - Brighton & Hove Albion 2:1
Runcorn FC - Wellington Town 3:0
Torquay United - Exeter City 3:1
Workington AFC - Mansfield Town 1:1
Walthamstow Ave - Tunbridge Wells 4:1
Aldershot FC - Guildford City 1:1
Horden Colliery Welfare ACF - Chorley FC 1:1
North Shields FC - Stockport County 1:4
Chelmsford City - Kidderminster Harriers 4:0
28/11/1938 Queens Park Rangers - Crystal Palace 3:0
29/11/1938 Southport FC - Scarborough FC 5:3
30/11/1938 Crewe Alexandra - Oldham Athletic 1:0
Cardiff City - Cheltenham Town 1:0
Mansfield Town - Workington AFC 2:1
Guildford City - Aldershot FC 3:4
Chorley FC - Horden Colliery Welfare ACF 1:2
05/12/1938 Newport County - Reading FC 3:1
2. Round
10/12/1938 Horden Colliery Welfare ACF - Newport County 2:3
Chelmsford City - Darlington FC 3:1
Runcorn FC - Aldershot FC 3:1
Southport FC - Swindon Town 2:0
Halifax Town - Mansfield Town 1:1
Port Vale FC - Southport FC 0:1
Cardiff City - Crewe Alexandra 1:0
Scunthorpe & Lindsey - Watford FC 1:2
Hartlepools United - Queens Park Rangers 0:2
Bristol Rovers - Bournemouth and Boscombe Athletic 0:3
Stockport County - Walthamstow Ave 0:0
Ipswich Town - Torquay United 4:1
Gainsborough Trinity - Doncaster Rovers 0:1
Lincoln City - Bromley FC 8:1
Folkestone Invicta - Yeovil & Petters United 1:1
Walsall FC - Clapton Orient 4:2
Chester City - Hull City 2:2
15/12/1938 Walthamstow Ave - Stockport County 1:3
Yeovil & Petters United - Folkestone Invicta 1:0
Hull City - Chester City 0:1
19/12/1938 Mansfield Town - Halifax Town 3:3
Halifax Town - Mansfield Town 0:0
21/12/1938 Mansfield Town - Halifax Town 1:2
3. Round
07/01/1939 Birmingham FC - Halifax Town 2:0
Blackpool FC - Sheffield United 1:2
Chester City - Coventry City 1:0
Liverpool FC - Luton Town 3:0
Leicester City - Stoke City 1:1
Notts County - Burnley FC 3:1
Blackburn Rovers - Swansea Town 2:0
Aston Villa - Ipswich Town 1:1
Sheffield Wednesday - Yeovil & Petters United 1:1
Wolverhampton Wanderers - Bradford Park Avenue 3:1
Middlesbrough FC - Bolton Wanderers 0:0
West Bromwich Albion - Manchester United 0:0
Sunderland AFC - Plymouth Argyle 3:0
Derby County - Everton FC 0:1
Tottenham Hotspur - Watford FC 7:1
Queens Park Rangers - West Ham United 1:2
Fulham FC - Bury FC 6:0
Barnsley FC - Stockport County 1:2
Brentford FC - Newcastle United 0:2
Portsmouth FC - Lincoln City 4:0
Chelsea FC - Arsenal FC 2:1
Cardiff City - Charlton Athletic 1:0
Newport County - Walsall FC 0:2
Runcorn FC - Preston North End 2:4
Chelmsford City - Southampton FC 4:1
10/01/1939 Grimsby Town - Tranmere Rovers 6:0
Southport FC - Doncaster Rovers 1:1
11/01/1939 Chesterfield FC - Southend United 1:1
Huddersfield Town - Nottingham Forest 0:0
Leeds United - Bournemouth and Boscombe Athletic 3:1
York City - Millwall FC 0:5
12/01/1939 Norwich City - Manchester City 0:5
11/01/1939 Manchester United - West Bromwich Albion 1:5
Bolton Wanderers - Middlesbrough FC 0:0
Ipswich Town - Aston Villa 1:2
Stoke City - Leicester City 1:2
12/01/1939 Doncaster Rovers - Southport FC 2:1
Yeovil & Petters United - Sheffield Wednesday 1:2
16/01/1939 Nottingham Forest - Huddersfield Town 0:3
Southend United - Chesterfield FC 4:3
Bolton Wanderers - Middlesbrough FC 0:1
4. Round
21/01/1939 Birmingham FC - Chelmsford City 6:0
Blackburn Rovers - Southend United 4:2
Cardiff City - Newcastle United 0:0
Chelsea FC - Fulham FC 3:0
Everton FC - Doncaster Rovers 8:0
Leeds United - Huddersfield Town 2:4
Liverpool FC - Stockport County 5:1
Middlesbrough FC - Sunderland AFC 0:2
Millwall FC - Grimsby Town 2:2
Notts County - Walsall FC 0:0
Portsmouth FC - West Bromwich Albion 2:0
Preston North End - Aston Villa 2:0
Sheffield United - Manchester City 2:0
Sheffield Wednesday - Chester City 1:1
West Ham United - Tottenham Hotspur 3:3
Wolverhampton Wanderers - Leicester City 5:1
24/01/1939 Grimsby Town - Millwall FC 3:2
25/01/1939 Chester City - Sheffield Wednesday 1:1
Newcastle United - Cardiff City 4:1
26/01/1939 Walsall FC - Notts County 4:0
30/01/1939 Tottenham Hotspur - West Ham United 1:1
Sheffield Wednesday - Chester City 2:0
02/02/1939 West Ham United - Tottenham Hotspur 2:1
Round of 16
11/02/1939 Birmingham FC - Everton FC 2:2
Chelsea FC - Sheffield Wednesday 1:1
Huddersfield Town - Walsall FC 3:0
Newcastle United - Preston North End 1:2
Portsmouth FC - West Ham United 2:0
Sheffield United - Grimsby Town 0:0
Sunderland AFC - Blackburn Rovers 1:1
Wolverhampton Wanderers - Liverpool FC 4:1
13/02/1939 Sheffield Wednesday - Chelsea FC 0:0
14/02/1939 Grimsby Town - Sheffield United 1:0
15/02/1939 Everton FC - Birmingham FC 2:1
16/02/1939 Blackburn Rovers - Sunderland AFC 0:0
20/02/1939 Blackburn Rovers - Sunderland AFC 1:0 aet
Chelsea FC - Sheffield Wednesday 3:1
Quarter-finals
04/03/1939 Chelsea FC - Grimsby Town 0:1
Huddersfield Town - Blackburn Rovers 1:1
Portsmouth FC - Preston North End 1:0
Wolverhampton Wanderers - Everton FC 2:0
09/03/1939 Blackburn Rovers - Huddersfield Town 1:2
Semi-finals
25/03/1939 Portsmouth FC - Huddersfield Town 2:1
Wolverhampton Wanderers - Grimsby Town 5:0
Final
29/04/1939 Portsmouth FC - Wolverhampton Wanderers 4:1 (2:0)